13534-97-9

Basic information

• Product Name: 5-Amino-2-bromopyridine
• Synonyms: TIMTEC-BB SBB005540;TIMTEC-BB SBB003823;LABOTEST-BB LT00129606;2-BROMO-5-AMINOPYRIDINE;5-BROMO-2-AMINOPYRIDINE;5-AMINO-2-BROMOPYRIDINE;3-AMINO-6-BROMOPYRIDINE;AKOS BBS-00004444
• CAS NO: 13534-97-9
• Molecular Formula: C₅H₅BrN₂
• Molecular Weight: 173.01
• EINECS: 214-019-9
• Product Categories: pyridines;Amines;blocks;Bromides;Pyridine;pyridine derivative;Amines and Anilines;Heterocycles;pharmacetical;Pyridine series;Chemical Amines;Bromopyridines;Halopyridines;Aromatics;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Amino-pyridine series;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 13534-97-9.mol
• Article Data: 24

Chemical Properties

• Melting Point: 75 °C
• Boiling Point: 180 °C
• Flash Point: 129.9 °C
• Appearance: Beige to brown-black/Powder
• Density: 1.6065 (rough estimate)
• Vapor Pressure: 0.00198mmHg at 25°C
• Refractive Index: 1.5182 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 1.87±0.10(Predicted)
• BRN: 109102
• CAS DataBase Reference: 5-Amino-2-bromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-2-bromopyridine(13534-97-9)
• EPA Substance Registry System: 5-Amino-2-bromopyridine(13534-97-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 13534-97-9(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow needles

Uses

3-Amino-6-bromopyridine may undergo polymerization via Buchwald–Hartwig amination in the presence of sodium tert-butoxide and XPhos(2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl) ligand yielding para-linked and meta-linked polyaminopyridines.

General Description

3-Amino-6-bromopyridine can be synthesized via bromination of 3-aminopyridine using N-bromosuccinimide in acetonitrile.

InChI:InChI=1/C5H5BrN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2

Upstream product

• 4487-59-6 2-bromo-5-nitropyridine 
• 462-08-8 pyridin-3-ylamine 
• 7439-89-6 iron 
• 4214-76-0 5-nitro-pyridin-2-ylamine 
• 5418-51-9 5-nitro-2-hydroxypyridine 

Downstream Products

• 934266-82-7 5-bromothiazolo[5,4-b]pyridin-2-amine 
• 462-08-8 pyridin-3-ylamine 
• 1026901-65-4 2-(5-amino-pyridin-2-yl)-N-tert-butyl-benzenesulfonamide 
• 1026846-32-1 [5-[6-(2-tert-butylsulfamoyl-phenyl)-pyridin-3-ylcarbamoyl]-3-(3-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid methyl ester 
• 218594-15-1 tert-butyl (6-bromopyridin-3-yl)carbamate 
• 13797-77-8 5-methoxythiazolo[5,4-b]pyridin-2-amine 
• 945746-53-2 C₁₂H₈ClF₃N₂ 
• 1275993-34-4 ethyl 4-(5-amino-2,3'-bipyridin-6'-yloxy)cyclohexanecarboxylate 
• 1246612-59-8 benzyl 6-bromo-2-methyl-1,2,3,4-tetrahydro-1,5-naphthyridin-4-yl-carbamate 
• 126370-67-0 6-phenylpyridin-3-amine 
• 1579294-53-3 5-(2-methoxyphenylselanyl)-2-bromopyridine 
• 1454925-54-2 3-(3-(4-(5-aminopyridin-2-yl)phenyl)propyl)-1-(4-(tert-butyl)benzyl)-4-ethyl-1H-1,2,4-triazol-5(4H)-one 

Relevant articles and documents

Metal-Free, Rapid, and Highly Chemoselective Reduction of Aromatic Nitro Compounds at Room Temperature

In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4′-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

REACTION COMPOSITION AND REACTION SYSTEM USING THIS

An aromatic nitro compound has a structure in which a nitro group and a halogen atom, in a separated state, are directly bonded as substituents to the ring structure of the same ring; a reaction composition is provided which, in a hydrogenation reaction of the nitro group of said aromatic nitro compound, allows selectively hydrogenating the nitro group, and sufficiently reducing the separation of the halogen atom from the ring; also provided is a reaction system that uses this reaction composition. This reaction composition includes a solvent, and a catalyst which, with the aforementioned aromatic nitro compound as reactant, is used in a hydrogenation reaction of at least one of the one or more nitro groups of said reactant. The catalyst includes a carrier, and Fe oxide particles and Pt particles supported by the carrier.

Cu-mediated selective bromination of aniline derivatives and preliminary mechanism study

A simple and efficient bromination of aniline, aniline derivatives, and analogs have been developed. Forty three examples were given and the highest yield reached was 98%. Different substrates including substituted aniline, pyridin-amine, N-substituted aniline, N,N-disubstituted aniline, N-phenyl-amide, N-phenyl-sulfonamide, and nitrogen-containing heterocycles were all reactive and selectively generated desired bromo-products. The method can be applied to synthesize drug intermediate and quinoxaline derivatives.